Our trip to CN December of 2011 began with a 6:00 a.m. flight, direct to Montego Bay, TimAir flight to Negril, drink in hand at the CN pool bar at 11:26 a.m. (not bad for a travel day ).
My wife is about to book our flights for April 2013. 7:00 a.m. flight, but the time difference works in our favor to arrive in Montego Bay at 9:56 a.m. We will take TimAir again and hope to break our record by having a drink in hand at the pool bar before 11:26 a.m.! (I try not to think about the back end of the trip, but the return flight is pretty sweet, too, with a 3:55 p.m. departure - enough time for lunch before we leave)
We are in central NJ, so we have lots of airports around (Newark, JFK, LaGuardia, Phili). We flew Caribbean Air out of Phili when we set "the record". We are a little reluctant to fly them though because they have been known to cancel flights. Most flights have been out of Newark, Continental (now United) direct to Montego Bay. We flew Delta once - never again (one stop in Atlanta, they canceled the leg to Montego Bay, provided ZERO assistance other than saying "no options...you are staying in Atlanta tonight"...so we found seats on an AirTran flight and made it to CN that day in spite of Delta's complete lack of customer service...sorry for the rant). This spring we are looking at Jet Blue, direct from JFK.
My wife does all of the searching and booking. She is pretty good at finding various options (time, location, price) and finding the flight that works best for us. Getting there early on day 1 and leaving late on the last day is the best!